As the 1990s came to a close, NASCAR welcomed a new 1999 Winston Cup champion in Dale Jarrett -- of course, after a season-long battle with Bobby Labonte and Mark Martin. The 1999 NASCAR Winston Cup season was also notable for the arrival of a new fleet of young drivers, and freshman Tony Stewart led the charge by winning three races in his first season on the track. See the winners and other details of all the season's races with the 1999 NASCAR Winston Cup results chart that follows.
 Jeff Gordon (#24), Dale Earnhardt (#3), and Jeff Burton (#99) race three abreast toward the end of the 1999 Daytona 500, a NASCAR Winston Cup series event that Gordon would eventually win. See more pictures of NASCAR. |
1999 NASCAR Winston Cup Results
| Number | Date | Site | Race Winner | Car | Speed |
| 1 | 2/14/99 | Daytona Beach, FL | Jeff Gordon | Chevy | 161.551 |
| 2 | 2/21/99 | Rockingham, NC | Mark Martin | Ford | 120.750 |
| 3 | 3/07/99 | Las Vegas, NV | Jeff Burton | Ford | 137.537 |
| 4 | 3/14/99 | Atlanta, GA | Jeff Gordon | Chevy | 143.284 |
| 5 | 3/21/99 | Darlington, SC | Jeff Burton | Ford | 121.294 |
| 6 | 3/28/99 | Ft. Worth, TX | Terry Labonte | Chevy | 144.276 |
| 7 | 4/11/99 | Bristol, TN | Rusty Wallace | Ford | 93.363 |
| 8 | 4/18/99 | Martinsville, VA | John Andretti | Pontiac | 75.653 |
| 9 | 4/25/99 | Talladega, AL | Dale Earnhardt | Chevy | 163.395 |
| 10 | 5/02/99 | Fontana, CA | Jeff Gordon | Chevy | 150.276 |
| 11 | 5/15/99 | Richmond, VA | Dale Jarrett | Ford | 100.102 |
| 12 | 5/30/99 | Charlotte, NC | Jeff Burton | Ford | 151.367 |
| 13 | 6/06/99 | Dover, DE | Bobby Labonte | Pontiac | 120.603 |
| 14 | 6/13/99 | Brooklyn, MI | Dale Jarrett | Ford | 173.997 |
| 15 | 6/20/99 | Pocono, PA | Bobby Labonte | Pontiac | 118.898 |
| 16 | 6/27/99 | Sonoma, CA | Jeff Gordon | Chevy | 70.378 |
| 17 | 7/03/99 | Daytona Beach, FL | Dale Jarrett | Ford | 169.213 |
| 18 | 7/11/99 | Loudon, NH | Jeff Burton | Ford | 101.876 |
| 19 | 7/25/99 | Pocono, PA | Bobby Labonte | Pontiac | 116.982 |
| 20 | 8/07/99 | Indianapolis, IN | Dale Jarrett | Ford | 148.194 |
| 21 | 8/15/99 | Watkins Glen, NY | Jeff Gordon | Chevrolet | 87.722 |
| 22 | 8/22/99 | Brooklyn, MI | Bobby Labonte | Pontiac | 144.332 |
| 23 | 8/28/99 | Bristol, TN | Dale Earnhardt | Chevrolet | 91.276 |
| 24 | 9/05/99 | Darlington, SC | Jeff Burton | Ford | 107.816 |
| 25 | 9/11/99 | Richmond, VA | Tony Stewart | Pontiac | 104.006 |
| 26 | 9/19/99 | Loudon, NH | Joe Nemechek | Chevrolet | 100.673 |
| 27 | 9/26/99 | Dover, DE | Mark Martin | Ford | 127.434 |
| 28 | 10/03/99 | Martinsville, VA | Jeff Gordon | Chevrolet | 72.624 |
| 29 | 10/10/99 | Charlotte, NC | Jeff Gordon | Chevrolet | 160.306 |
| 30 | 10/17/99 | Talladega, AL | Dale Earnhardt | Chevrolet | 166.632 |
| 31 | 10/24/99 | Rockingham, NC | Jeff Burton | Ford | 131.103 |
| 32 | 11/07/99 | Phoenix, AZ | Tony Stewart | Pontiac | 118.132 |
| 33 | 11/14/99 | Homestead, FL | Tony Stewart | Pontiac | 140.335 |
| 34 | 11/21/99 | Atlanta, GA | Bobby Labonte | Pontiac | 137.932 |
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